Already a leader in the edtech space since its 2008 launch, Khan Academy was now one of the first edtech organizations to embrace generative artificial intelligence ("genAI"). In March 2023, Khan Academy began beta testing Khanmigo, a genAI "guide" and tutor built with ChatGPT, a technology developed by the San Francisco-based AI research lab OpenAI. In addition to simulating historical and fictional characters, Khanmigo assisted students with learning math, debugging code, writing, and completing other learning exercises. Khanmigo was also designed to help teachers develop lesson plans and quizzes, brainstorm creative teaching approaches, and evaluate students' progress, among other tasks. As the Founder and CEO of Khan Academy, Sal Khan felt that Khanmigo might just be "that holy grail we've all been reading about in science fiction for years, about an artificial intelligence that could emulate a human tutor." However, he pondered what the societal-and, for Khan Academy, organizational-risks might be of using OpenAI's ChatGPT. Was it possible that Khanmigo would introduce new problems or exacerbate existing problems in classrooms around the world? If so, what more could Khan Academy do to prevent such outcomes? How might Khan Academy itself need to evolve to support and shepherd this new tool? At the most extreme, might genAI increase Khan Academy's impact manifold, or might the new technology diminish its impact?

San Francisco based Vida Health, founded by Stephanie Tilenius, former vice president of Commerce and Payments at Google, was a B2B digital health startup focused on the treatment of cardiometabolic conditions, such as diabetes and obesity. Its innovative digital platform integrated technology with human care, and its treatment approach focused on physical health as and mental health, creating a unique, holistic solution. As a Series D venture backed company with $188 million in funding, Vida was eager to scale the business faster. In 2023 Tilenius was grappling with whether to start prescribing weight loss drugs as part of Vida's obesity management program. Consumer demand for newly FDA-approved semaglutide drugs (GLP-1s), like Ozempic, was surging. However, GLP-1s were already facing scrutiny for risks; they had known negative side effects; and there was no clear scientific proof that people could be taken off them and maintain weight loss. It was also not clear how the market would respond if Vida-which had differentiated itself through its behavioral management approach to chronic disease-entered the weight loss prescription drug business. Would Vida be characterized as a "pill-mill"? If Vida did decide to offer prescription weight loss drugs as part of its platform, it would also have to decide if it should roll out a B2C platform to reach consumers who were not covered through an employer plan or whose plan did not cover weight loss medications. Tilenius had significant experience with B2C brands and saw the potential. However, building a B2C brand would likely be a costly endeavor.

In 2012, Evan Marwell launched EducationSuperHighway (ESH) to address a major problem: though most public K-12 schools in the US had access to the Internet, only roughly 30% had true broadband access that would enable every student to have high speed connectivity. Marwell and his team raised philanthropic capital and worked with schools, telecommunications companies, and local, state, and federal government officials to meet that challenge. By 2019, over 99% of the public schools in the US had true broadband access. Marwell and his team had begun the process of winding down activities at ESH when the pandemic erupted. Students were working from home, not physically at school. They decided to try to help 18 million households with 47 million people to have affordable broadband access at home. In 2020, Marwell and Jessica Reid Sliwerski also launched a program to tackle a pernicious problem in education; by third grade, only about one in three US children were reading at grade level. Ignite! Reading offered students access to an individual science of reading tutor for 15 minutes a day over Zoom while at school. Early evidence suggested that for every week working with an Ignite tutor, kids gained over 2 weeks of reading comprehension. Ignite was organized as a public benefit corporation.

As COVID-19 swept across the globe in 2020, the education sector faced unprecedented disruption. Schools and colleges worldwide shut down, forcing over a billion students and teachers to move to online learning. Investor interest in the EdTech space exploded as technology-based education solutions shifted from a "nice-to-have" to a "must-have." As one of the leading EdTech venture capital firms, GSV Ventures, which had backed industry leaders such as Coursera, ClassDojo, Guild Education, Remind, and Course Hero, was positioned to be at the forefront of the changes happening to education across the world. In light of the pandemic, GSV had to postpone and reenvision its hallmark ASU+GSV Summit - a partnership with Arizona State University and GSV that showcased the latest innovations and innovators across the global "pre-K to gray" EdTech space - that had been scheduled for March 30 to April 1. However, on the positive side, GSV Ventures was facing a surge in investor interest in its Fund II which had begun fundraising in 2019. The original target had been to raise $100 million, but there was recent discussion of increasing Fund II to $200 to $250 million. Quazzo needed to decide whether it made sense to expand the fund, and if so, what changes would need to be made internally and strategically to support a larger fund. At a higher level, Quazzo wondered whether the momentum gained in EdTech during the first few months of COVID-19 was sustainable. Would the global focus on remote learning during the COVID-19 pandemic trigger systemic changes? Could this be a unique opportunity to address the massive challenges associated with inequality of access, opportunity, and outcomes?

QuantumScape CEO Jagdeep Singh juggles the many activities required to lead the next-generation battery pioneer. Founded in 2010, QuantumScape's mission was to develop new "solid-state" car batteries that would improve upon traditional lithium-ion batteries in key areas such as range, charging speed, durability, cost, and safety. Success, they believed, would accelerate the transition from gasoline-powered cars to electric vehicles. Between 2010 and late 2020, QuantumScape operated in stealth mode and raised venture financing totaling more than $800 million. The team grew to over 200 employees, nearly all scientists and engineers working on the technical challenges associated with creating a solid-state battery that could be produced at scale. By summer 2020 it was clear to Singh and the board that the company required more capital to help fund its commercialization plan. In November 2020, QuantumScape went public by merging with a Special Purpose Acquisition Company (SPAC). Now, with that capital in hand, production facilities under construction, and a signed joint venture with Volkswagen, Singh expected to see cars with its batteries on highways by 2025.

Chia Network developed a novel blockchain platform that was more eco-friendly, decentralized, and scalable than Bitcoin, Ethereum, and other blockchains. Now, company leadership must decide how to scale the startup and prioritize various partnerships, use cases, and markets.

Founded in 2015, Guild Education is an education marketplace that connects employers and universities to provide employees with 'education as a benefit.' The Denver-based company is transforming traditional tuition assistance programs by facilitating direct payment by the employer to the academic institution and by supporting students with coaching and advising. By October 2020, Guild had gained market traction and demonstrated impressive results. Rachel Carlson, CEO and cofounder of Guild, must decide how to manage the company's future growth. She believes there is great potential within its core education marketplace to expand the network of academic institutions and portfolio of company partners. Carlson also envisions extending the business model and entering the career placement market. To successfully do that, she needs to find the same incentive alignment in these new businesses as in Guild's core education platform. Would it be possible to find a solution that would result in a win-win outcome for all?

Founded in 2008, Khan Academy was a global educational nonprofit with a mission to provide a free, world-class education for anyone anywhere in the world. By 2018, the organization had expanded into numerous content areas, product areas, and geographic markets. However, a newly minted 3-year strategic plan called for greater focus and prioritization to enable the young organization to maximize its impact. It also called for increased fundraising efforts to ensure long-term sustainability. The case poses several questions: how to balance Khan Academy's far-reaching aspirational vision for transforming education globally with the short term need for greater focus? Would the priorities set in the strategic plan enable Khan Academy to create systemic global change? How should donors evaluate the attractiveness and impact of a potential investment in Khan Academy relative to other organizations in the educational market? Was Khan Academy on the right path to ensuring long-term sustainability?

Founded in 2008, Khan Academy was a global educational nonprofit with a mission to provide a free, world-class education for anyone anywhere in the world. By 2018, the organization had expanded into numerous content areas, product areas, and geographic markets. However, a newly minted 3-year strategic plan called for greater focus and prioritization to enable the young organization to maximize its impact. It also called for increased fundraising efforts to ensure long-term sustainability. The case poses several questions: how to balance Khan Academy's far-reaching aspirational vision for transforming education globally with the short term need for greater focus? Would the priorities set in the strategic plan enable Khan Academy to create systemic global change? How should donors evaluate the attractiveness and impact of a potential investment in Khan Academy relative to other organizations in the educational market? Was Khan Academy on the right path to ensuring long-term sustainability?

The case explores the attempt of Shervin Pishevar, a prominent Silicon Valley investor, to shepherd hyperloop, a futuristic pod-in-tube transportation technology, from concept to transformative reality via Hyperloop One and Sherpa Capital, both companies he co-founded. The case outlines the technology-first brought to widespread attention by Tesla and SpaceX executive Elon Musk-then follows Pishevar as he builds a team, develops prototypes, recruits investors and partners, and navigates the many obstacles in pursuit of this "moonshot." Students are presented wih historical parallels and precedents that may illuminate certain aspects of the challenge.

Based in Portola Valley, California, WTI specialized in this hybrid form of debt and equity financing for early-stage companies. Like traditional venture capital and private equity firms, WTI raised funds from institutional investors and evaluated deals. However, instead of making initial investments in the form of equity, WTI focused primarily on lending money to start-ups, charging them interest and receiving warrants that could later be converted to stock in the case of a liquidity event. Most initial investments-usually in the range of $3-$5 million-were made in tandem with or following a company's early rounds of venture capital equity financing. In addition, like more traditional venture capital investors, WTI hoped to participate in follow-on debt and equity investments in its successful portfolio companies.

The case describes Rubicon Global, a startup that aimed to disrupt the waste management industry. The company started with a bold idea: create a cloud-based, full-service waste management company providing low-cost, highly efficient, and environmentally friendly service anywhere in the country through a national network of independent waste haulers and recyclers. A player in the sharing economy, Rubicon was developing an on-demand mobile application that did for waste management what Uber had done for taxi service. Rubicon had made great progress since introducing its service. They had signed up large multi-national customers and had a number of large potential contracts in the negotiation phase. The team needed more capital to build out the network and technology platform. Management and the board had to make a number of critical decisions: how much should the company raise, for what purpose, from whom, and on what terms?

The UPower founders, Jake DeWitte and Caroline Cochran, were recent graduates from MIT's Nuclear Science and Engineering Department. They chose to attend Palo Alto-based Y Combinator's accelerator program to focus on building a "mini" nuclear reactor that would produce up to ten MW of power and could fit in two 40-foot intermodal shipping containers. The UPower reactor was designed to serve the need for "off-grid" electric power. These off-grid customers were in remote locations such as mining operations, military bases, Arctic townships or even island nations. While DeWitte and Cochran were ecstatic about the progress they had made and the enthusiastic open-mindedness of Bay Area investors to backing groundbreaking and even potentially contentious "big ideas," they wondered if their investors would have the patience to finance UPower over the long term.